3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Temperature

0 °C

In a dry round-bottomed flask, 1-Boc-3-azetidinone (0.70 g, 4.1 mmol) was dissolved in THF (20 mL). The solution was cooled to 0° C. and methylmagnesium chloride (3.0 M solution in THF, 2.0 mL, 6.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with 10 mL saturated NH4Cl, diluted with 5 mL water and extracted with 100 mL EtOAc (2×). The combined organic layers were washed with 10 mL water and 10 mL brine then combined, dried over sodium sulfate, filtered and concentrated to afford 757 mg (99%) of 3-hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester as an off-white solid.

1. customThe reaction mixture was quenched with 10 mL saturated NH4Cl
2. additiondiluted with 5 mL water
3. extractionextracted with 100 mL EtOAc (2×)
4. washThe combined organic layers were washed with 10 mL water and 10 mL brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-8323827707c54ca6a5d06fc443abbb4d

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2